Sodium Hydroxide → HCID 57748288, compound

HRID 906198Notes

Reaction equation

HRID 906198 reaction equation
[NH2:1][C:2]([C:4]1[C:13]([NH:14][CH:15]([CH2:18][CH3:19])[CH2:16][CH3:17])=[CH:12][C:7]([C:8]([O:10]C)=[O:9])=[C:6]([C:20]([F:23])([F:22])[F:21])[CH:5]=1)=[O:3].[OH-].[Na+]>CO>[NH2:1][C:2]([C:4]1[C:13]([NH:14][CH:15]([CH2:16][CH3:17])[CH2:18][CH3:19])=[CH:12][C:7]([C:8]([OH:10])=[O:9])=[C:6]([C:20]([F:21])([F:22])[F:23])[CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67404491HCID 67404491, compound

Product 1

HCID 57748288HCID 57748288, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-aminocarbonyl-5-(pentan-3-ylamino)-2-(trifluoromethyl)benzoate (0.818 mmol) was dissolved in methanol (2 mL) and was treated with 2M sodium hydroxide (1 mL, 2 mmol) at 45° C. for 1.5 h. The reaction mixture was cooled to ambient temperature and was concentrated to afford an aqueous residue that was washed with ether, then cooled in an ice bath and acidified with 1N hydrochloric acid to pH ˜3. The precipitate was collected by filtration, washed with water, then dried to afford 4-aminocarbonyl-5-(pentan-3-ylamino)-2-(trifluoromethyl)benzoic acid (233 mg, 0.733 mmol, 90% yield over 2 steps). 1H NMR (400 MHz, d6-DMSO): δ 13.5 (br s, 1H), 8.74 (d, 1H), 8.21 (br s, 1H), 7.95 (s, 1H), 7.46 (br s, 1H), 6.94 (s, 1H), 3.51-3.43 (m, 1H), 1.63-1.51 (m, 2H), 1.51-1.39 (m, 2H), 0.87 (t, 6H); MS (EI) for C14H17F3N2O3: 319 (MH+).

Workup

  1. concentrationwas concentrated
  2. customto afford an aqueous residue that
  3. washwas washed with ether
  4. temperaturecooled in an ice bath
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-787fe0fdbdf7477ebedba7b1dbe2cac8
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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